2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one → HCID 19921931, compound

HRID 1648040Notes

Reaction equation

HRID 1648040 reaction equation
C[O:2][C:3](=[O:19])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.[OH:20][C:21]1[CH:31]=[CH:30][C:24]2[C:25](=[O:29])[CH2:26][CH2:27][O:28][C:23]=2[C:22]=1[CH2:32][CH2:33][CH3:34]>>[O:29]=[C:25]1[C:24]2[CH:30]=[CH:31][C:21]([O:20][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3/[CH:5]=[CH:4]/[C:3]([OH:2])=[O:19])=[C:22]([CH2:32][CH2:33][CH3:34])[C:23]=2[O:28][CH2:27][CH2:26]1

Participants

3

Reactant 2

HCID 153182992,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-oneHCID 67780233HCID 67780233, compound

Product 1

HCID 19921931HCID 19921931, compound

Procedure

Using the procedure of example 4, and starting with 0.5 g (1.5 mmol) of (E)-3-[2-[(5-bromopentyl)oxy]phenyl]-2-propenoic acid methyl ester and 0.3 g (1.45 mmol) of 2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one, (E)-3-[2-[5-[(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)oxy]pentyloxy]phenyl]-2-propenoic acid was obtained in 24% overall yield after purification by flash chromatography (silica gel, chloroform-methanol-acetic acid) and recrystallization from acetonitrile as a colorless solid, mp 123°-126° C.

Sources & evidence

ORD record
ord-01021b634cf94c7486e88b027857c0ca
Source dataset
uspto-grants-1995_07
Patent number
US05434186

Reaction notes

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